1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux 3: 5 palladium on charcoal; hydrogen / ethyl acetate / 760.05 Torr 4: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / toluene / 15 - 20 °C 5: acetic acid; zinc / methanol / 0.5 h / |Reflux 6: trifluoroacetic acid / dichloromethane / 20 °C 7: sodium hydrogencarbonate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C View Scheme

1: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / |Inert atmosphere 2: hydrogen; palladium(II) oxide hydrate / methanol / 1 h / 20 °C / 1034.32 Torr / |Inert atmosphere 3: dicyclohexyl-carbodiimide; 4-(N,N-dimethlyamino)pyridine; toluene-4-sulfonic acid / dichloromethane / 20 °C / |Inert atmosphere 4: acetyl chloride / tetrahydrofuran; methanol / 2 h / 0 °C / |Inert atmosphere View Scheme

1: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / |Inert atmosphere 2: hydrogen; palladium(II) oxide hydrate / methanol / 1 h / 20 °C / 1034.32 Torr / |Inert atmosphere View Scheme

Multi-step reaction with 6 steps 1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux3: 5 palladium on charcoal; hydrogen / ethyl acetate / 760.05 Torr4: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / toluene / 15 - 20 °C5: acetic acid; zinc / methanol / 0.5 h / |Reflux6: trifluoroacetic acid / dichloromethane / 20 °C  

Multi-step reaction with 3 steps 1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux3: 5 palladium on charcoal; hydrogen / ethyl acetate / 760.05 Torr  

Multi-step reaction with 2 steps 1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux  

Multi-step reaction with 4 steps 1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / |Reflux3: 5 palladium on charcoal; hydrogen / ethyl acetate / 760.05 Torr4: 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide / toluene / 15 - 20 °C